Malonic Acid → 3-Amino-3-(4-fluorophenyl)propanoic acid

HRID 916175Notes

Reaction equation

HRID 916175 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O-:13])(=[O:12])[CH3:11].[NH4+:14].C(O)(=O)CC(O)=O>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([CH2:11][C:10]([OH:13])=[O:12])[NH2:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 680234-FluorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 5798853-Amino-3-(4-fluorophenyl)propanoic acidYield 68.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Fluorobenzaldehyde (10 g, 80 mmol), ammonium acetate (8.2487 g, 107 mmol) and malonic acid (8.3285 g, 80 mmol) were refluxed (slow) in absolute ethanol (60 mL) for 48 hours. White solid was filtered and purified by ethanol recrystallization to afford β-4-fluorophenyl-β-alanine (10.04 g, 54.8 mmol, 68.5%); MP: 216-217° C.; IR (KBr): 3160, 1606 cm−1; TLC: RF=0.41 (solvent 24), 0.42 (solvent 25); 1H NMR (D2O/K2CO3): δ 7.28-7.19 (m, 2H), 7.03-6.91 (m, 2H), 4.10 (t, J=7.39 Hz, 1H), 2.54-2.34 (m, 2H). Anal. Calcd for C9H10FNO2.5/3H2O: C, 50.70; H, 6.30; N, 6.57. Found: C, 50.34; H, 6.39; N, 6.30.

Workup

  1. filtrationWhite solid was filtered
  2. custompurified by ethanol recrystallization

Sources & evidence

ORD record
ord-aeb9d77789e44df3ab74d9a2e0f0dd6b
Source dataset
uspto-grants-2007_09
Patent number
US07268164B2

Reaction notes

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